diff --git a/api/server/routes/convos.js b/api/server/routes/convos.js
index a45d32c212..8b0ec0a1e1 100644
--- a/api/server/routes/convos.js
+++ b/api/server/routes/convos.js
@@ -493,6 +493,9 @@ async function runImportJob(context, job) {
       filepath: job.filepath,
       userId,
       tenantId,
+      /** The same deadline the builder stamps on this import's conversations
+       * and messages, so an attachment expires with the chat that shows it. */
+      expiredAt: batch.getRetentionFields().expiredAt,
       format: target.format,
       defaultModel,
       deps: { saveBuffer, createFile: db.createFile, deleteFile: releaseAsset },
diff --git a/packages/api/src/import/assets.spec.ts b/packages/api/src/import/assets.spec.ts
index 30255b70ef..65f25e8431 100644
--- a/packages/api/src/import/assets.spec.ts
+++ b/packages/api/src/import/assets.spec.ts
@@ -818,3 +818,54 @@ describe('ingestAssets storage strategy', () => {
     expect(sources).toEqual(['document_backend']);
   });
 });
+
+/** Under `retentionMode: all` the batch builder gives imported conversations
+ * and messages a deadline. An attachment without the same deadline outlives
+ * the chat that shows it, in exactly the deployments that require everything
+ * to expire. */
+describe('ingestAssets retention', () => {
+  const archive: Archive = {
+    entries: [{ name: 'png-one.dat', bytes: 4 }],
+    read: async () => Buffer.from([0x89, 0x50, 0x4e, 0x47]),
+    close: () => undefined,
+  };
+
+  async function ingestWith(expiredAt?: Date) {
+    const rows: Array<{ expiredAt?: Date }> = [];
+    await ingestAssets({
+      archive,
+      layout: resolveLayout(archive.entries, null),
+      userId: 'u1',
+      tenantId: undefined,
+      expiredAt,
+      pointers: ['file-service://png-one'],
+      deps: {
+        saveBuffer: async ({ fileName }) => ({
+          filepath: `/uploads/u1/${fileName}`,
+          source: 'local',
+        }),
+        createFile: async (data) => {
+          rows.push(data);
+          return { file_id: data.file_id };
+        },
+      },
+    });
+    return rows;
+  }
+
+  it('stamps the retention deadline on the imported file row', async () => {
+    const expiredAt = new Date('2030-01-01T00:00:00.000Z');
+
+    const rows = await ingestWith(expiredAt);
+
+    expect(rows).toHaveLength(1);
+    expect(rows[0].expiredAt).toEqual(expiredAt);
+  });
+
+  it('leaves the row without a deadline when the deployment sets none', async () => {
+    const rows = await ingestWith(undefined);
+
+    expect(rows).toHaveLength(1);
+    expect(rows[0]).not.toHaveProperty('expiredAt');
+  });
+});
diff --git a/packages/api/src/import/assets.ts b/packages/api/src/import/assets.ts
index 0f61f64699..8510ac2e46 100644
--- a/packages/api/src/import/assets.ts
+++ b/packages/api/src/import/assets.ts
@@ -39,6 +39,8 @@ export interface CreateFileInput {
   source: string;
   context: string;
   tenantId?: string;
+  /** Retention deadline, when the deployment sets one. */
+  expiredAt?: Date;
 }
 
 export type CreateFileFn = (
@@ -63,6 +65,13 @@ export interface IngestInput {
   userId: string;
   tenantId: string | undefined;
   pointers: string[];
+  /** The retention deadline the conversations and messages of this import are
+   * getting. An imported attachment has to expire with the conversation that
+   * references it: without it the row and its storage object outlive the chat
+   * they belong to, in exactly the deployments that require everything to
+   * expire. `disableTTL` only suppresses the short upload TTL, which is a
+   * different field. */
+  expiredAt?: Date;
   deps: AssetDeps;
   /** Attachment metadata keyed by the raw id (pointer with its scheme
    * stripped). Supplies the authoritative `mime_type` the export recorded
@@ -304,6 +313,7 @@ async function ingestOne(
       source,
       context: FileContext.message_attachment,
       tenantId,
+      ...(input.expiredAt ? { expiredAt: input.expiredAt } : {}),
     },
     true,
   );
diff --git a/packages/api/src/import/claude/service.ts b/packages/api/src/import/claude/service.ts
index b5f4d56fd6..291ce1f926 100644
--- a/packages/api/src/import/claude/service.ts
+++ b/packages/api/src/import/claude/service.ts
@@ -130,6 +130,7 @@ export async function runClaudeImport(context: ProviderImportContext): Promise<v
       if (input.existingExternalIds.has(conv.uuid)) {
         report.skipped += 1;
         progress.conversations.done += 1;
+        await input.onProgress?.(progress);
         continue;
       }
 
diff --git a/packages/api/src/import/service.ts b/packages/api/src/import/service.ts
index 9012be78b8..8e807f0255 100644
--- a/packages/api/src/import/service.ts
+++ b/packages/api/src/import/service.ts
@@ -329,6 +329,7 @@ export async function runImport(input: RunImportInput): Promise<ImportReport> {
       layout,
       userId: input.userId,
       tenantId: input.tenantId,
+      expiredAt: input.expiredAt,
       pointers: scan.pointers,
       attachments: scan.attachments,
       references: scan.references,
@@ -374,6 +375,10 @@ export async function runImport(input: RunImportInput): Promise<ImportReport> {
         if (input.existingExternalIds.has(conv.conversation_id)) {
           report.skipped += 1;
           progress.conversations.done += 1;
+          /** Published like any other advance: re-importing a finished export
+           * is all skips, and without this the bar sits at its old value for
+           * the whole run and then jumps straight to completed. */
+          await input.onProgress?.(progress);
           continue;
         }
 
diff --git a/packages/api/src/import/sink.ts b/packages/api/src/import/sink.ts
index 8c56266eba..28390a6885 100644
--- a/packages/api/src/import/sink.ts
+++ b/packages/api/src/import/sink.ts
@@ -57,6 +57,10 @@ export interface RunImportInput {
   filepath: string;
   userId: string;
   tenantId?: string;
+  /** Retention deadline for everything this run writes, when the deployment
+   * sets one. The batch builder already applies it to conversations and
+   * messages; assets have to carry it too or they outlive the chats. */
+  expiredAt?: Date;
   defaultModel: string;
   /** The format `inspectExport` already identified. Omit it and `runImport`
    * re-reads the first shard to detect it. */